Ethyl 4-(4-methylphenyl)-4-oxobut-2-ynoate | 923286-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 4-(4-methylphenyl)-4-oxobut-2-ynoate
• 英文别名: ethyl 4-(4-methylphenyl)-4-oxobut-2-ynoate
• CAS: 923286-31-1
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: URVJITJCSCWMIW-UHFFFAOYSA-N

物化性质

• 沸点：
  333.4±35.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 4-(4-methylphenyl)-4-oxobut-2-ynoate 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 ethyl 9b-benzyl-2-(4-methylbenzoyl)-9bH-[1,4]oxathiino[2,3-b]indole-3-carboxylate
  参考文献：
  名称：

  A New Reaction Mode of 3-Halooxindoles: Acting as C–C–O Three-Atom Components for (3+3) Cycloaddition to Access Indolenine-Fused 2H-1,4-Oxathiines

  摘要：

  DOI：

  10.1021/acs.orglett.3c03745
• 作为产物：
  描述：

  ethyl 4-(4-methylphenyl)but-3-ynoate 在 二苯基二硒醚 、 水 、 三氟甲磺酸N-吡啶鎓 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以72%的产率得到Ethyl 4-(4-methylphenyl)-4-oxobut-2-ynoate
  参考文献：
  名称：

  炔烃的硒-π-酸催化氧化功能化：轻松获得壬和多取代的恶唑。

  摘要：

  公开了前所未有的硒催化炔烃的炔丙基氧化。各种炔丙基膦酸酯和3-链烷酸酯通过不寻常的CC三键迁移和乙烯基碳上的硒烯基化反应，有效地转化为有价值的炔酮。通过烯胺中间体的互变异构和S N 2置换的策略，相似的条件对于乙酰胺的氧化双官能化有效，从而提供了具有高区域选择性的多取代恶唑。机理研究揭示了这些详细的过程。

  DOI：

  10.1021/acscatal.8b01595

文献信息

• Chiral N,N′-dioxide/Sc(OTf)₃ complex-catalyzed asymmetric dearomatization of β-naphthols
  作者：Shulin Ge、Tengfei Kang、Lili Lin、Xiying Zhang、Peng Zhao、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c7cc06388a

  日期：——

  An efficient N,N’-dioxide-scandium(III) complex catalytic system has been developed for the asymmetric dearomatization of β-naphthols through conjugate addition to alkynones. A variety of Z-predominated β-naphthalenone compounds were obtained in moderate to high yields with excellent enantioselectivities (up to 98% ee). Moreover, a possible transition state was proposed to explain the origin of the

  已经开发了一种有效的N，N'-二氧化-（III）络合物催化系统，用于通过将共轭物加成炔烃使β-萘酚不对称脱芳香化。以中等至高收率获得了许多Z为主的β-萘酮化合物，并具有出色的对映选择性（最高98％ee）。此外，提出了一种可能的过渡态来解释立体选择性的起源。
• Highly Efficient Asymmetric Synthesis of Chiral γ-Alkenyl Butenolides Catalyzed by Chiral <i>N,N</i>′-Dioxide–Scandium(III) Complexes
  作者：Jie Ji、Lili Lin、Qiong Tang、Tengfei Kang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acscatal.7b00590

  日期：2017.6.2

  The asymmetric synthesis of γ-alkenyl butenolides was accomplished by conjugated addition of butenolides to alkynones. Both terminal alkynones and nonterminal alkynones were applicable to the N,N′-dioxide–scandium(III) catalytic system. The corresponding products were obtained in good to excellent yields (up to 99%) with high E/Z ratios and high enantioselectivities (up to 98% ee). The novel methods

  γ-烯基丁烯化物的不对称合成是通过将丁烯化物共轭添加到炔烃中来完成的。末端炔基和非末端炔基均适用于N，N'-二氧化物-scan（III）催化体系。获得了具有高E / Z比和高对映选择性（高达98％ee）的高至极好产率（高达99％）的相应产品。构建γ-烯基丁烯化物和连续环氧化产物的新方法有助于构建具有生物活性的天然产物和合成中间体的核心结构。另外，一锅迈克尔加成/环氧化反应在我们的催化系统中表现良好。
• Concise Assembly of Highly Substituted Furan-Fused 1,4-Thiazepines and Their Diels−Alder Reactions with Benzynes
  作者：Hanfeng Ding、Yiping Zhang、Ming Bian、Weijun Yao、Cheng Ma

  DOI：10.1021/jo702299m

  日期：2008.1.1

  A facile and highly efficient three-component reaction of thiazole or benzothiazole carbenes, disubstituted ketenes, and activated alkynes is disclosed. With this methodology, a polysubstituted ring system containing furo[2,3-c]thiazepine core can be constructed from simple and readily accessible starting materials in good yields. The scope and limitation of this transformation were investigated in detail by using various thiazole carbene, ketene, and alkyne components. Furthermore, the synthetic utilities of these unique polyheterocyclic compounds were demonstrated via their Diels-Alder reactions with benzynes to furnish thiazepine-fused 7-oxanorbornadiene derivatives in excellent yields.
• A Ring-Expansion Methodology Involving Multicomponent Reactions: Highly Efficient Access to Polysubstituted Furan-Fused 1,4-Thiazepine Derivatives
  作者：Cheng Ma、Hanfeng Ding、Yiping Zhang、Ming Bian

  DOI：10.1002/anie.200602836

  日期：2006.11.27
• Copper-Catalyzed Decarboxylative Cascade Cyclization of Propargylic Cyclic Carbonates/Carbamates with Pyridinium 1,4-Zwitterionic Thiolates to Fused Polyheterocyclic Structures
  作者：Ting-Ting Li、Yong You、Ting-Jia Sun、Yan-Ping Zhang、Jian-Qiang Zhao、Zhen-Hua Wang、Wei-Cheng Yuan

  DOI：10.1021/acs.orglett.2c01959

  日期：2022.7.22